The Weeknd and Drake Are in a Windbreaker Battle

Colorful windbreakers—the kind worn by soccer coaches, sailors, your mom at the beach, and now The Weeknd—have seen an uptick in popularity of late. That's largely thanks to the commercial resurgence of nearly every major ’90s sportswear brand, and also to a combination of men who won't let the staple die. Shia LaBeouf's affection for vintage outerwear remains unbelievably strong, while rappers like Lil Yachty (a spokesman for Nautica), A$AP Rocky, and Drake regularly don the water-repellent jackets on- and offstage. So we didn't bat an eye when The Weeknd took to the streets of New York in a turquoise Puma windbreaker—that is, until we took a closer look.

The danger of buying in to the ’90s windbreaker trend is that it relies on the juxtaposition of a patently uncool clothing item with the rest of your extra-cool wardrobe. Not everyone (including otherwise stylish famous guys) comes out unscathed. There's definitely a way to wear a windbreaker without looking like you've just released an exercise workout on VHS, but The Weeknd hasn't found it.

Colorblocking on your windbreaker can add graphic pop to an all-black outfit—but if it's not well-placed, it can also make your body look broader and your arms appear delicate. The most flattering colorblock arrangement should set dark colors across the center of your torso and brighter/lighter colors on the sleeves and shoulders. That's because dark colors are slimming and lighter colors add visual heft. Sadly, The Weeknd's jacket does the opposite.

In contrast, fellow Canadian superstar Drake is long past the days of merely dipping his toe in the windbreaker pool. Drake's got a collection of lightweight inclement-weather jackets, most of which are more flattering than The Weeknd's teal cube. A devoted fan of the brand Stone Island, Drake leans toward windbreakers that are more minimal, usually in solid colors like black, white, red, and royal blue.

But it's not just the solid colors that make Drake's choice in windbreakers more flattering. When Drizzy's not wearing a vintage windbreaker like the all-red one above, he's wearing a modern take on it that boasts sturdier fabrics and cuts that feel way more 2017 than 1995: think trim rather than blousy. Chances are you're in the market for a lightweight fall jacket right now, so we'd like to steer you in the more stylish direction. And only one of these Canadians can help.